The Hardest Part of Running a Portfolio of Businesses

The Hardest Part of Running a Portfolio of Businesses

Lesson: Momentum Creates a New Kind of Challenge

I finally have several businesses gaining real traction, and with that momentum came one of the hardest decisions I’ve had to face: how to allocate my time and resources across the portfolio. Some businesses are performing incredibly well, others need support, and figuring out how to leverage the strong ones to lift the weaker ones has been a constant juggle. With over a dozen companies in my world, many of which support dozens more, prioritization has become its own discipline.

Insight: Time Allocation Is the CEO Skill No One Teaches You

• Momentum Isn’t Uniform: In a portfolio, businesses grow at different speeds. Treating them all equally is the fastest way to stall the entire system.
• Your Time Is the Rarest Resource: Money can be redeployed, talent can be hired, systems can scale. But your time is fixed, scarce, and the lever that matters most.
• Lift From Strength, Not Weakness: The best-performing businesses can create structure, cash flow, and stability that support the ones still finding product-market fit. Smart allocation compounds.

When you’re running multiple companies, the challenge isn’t building, it’s deciding where your energy moves the needle the most.

Action Item: Run a Portfolio Time Audit

1. Rank Your Businesses - Sort them into three buckets: thriving, stable, struggling.
2. Allocate Time by Impact, Not Emotion - Prioritize the companies where your involvement creates outsized leverage.
3. Create One System of Support - Use wins from the thriving group (cash flow, playbooks, talent) to stabilize the ones behind.

Growth doesn’t just require more effort, it requires better allocation. The bigger the portfolio, the sharper the discipline.

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